Reaktion #722646

Reaktionsgleichung

potassium hydroxide

hydrochloric acid

ethyl 2-(2-(2-benzyloxyphenyl)ethyl)-2-methoxycarbonylaminopentanoate

lithium borohydride

→

compound

Ausbeute 63.1%

2-Amino-2-(2-(2-benzyloxyphenyl)ethyl)pentanol

Ausbeute 63.1%

Lösungsmittel

tetrahydrofuran

methanol

water

water

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed
2. 2
   Temperaturunder heating for 2.5 hours
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with a saturated brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled away under reduced pressure
7. 7
   SonstigeThe residue obtained
8. 8
   Temperaturthe mixture was refluxed
9. 9
   Temperaturunder heating for 4 days
10. 10
    Extraktionextracted with ethyl acetate
11. 11
    WaschenThe organic layer was washed with a saturated brine
12. 12
    Trocknendried over sodium sulfate
13. 13
    workup.DISTILLATIONthe solvent was distilled away under reduced pressure
14. 14
    EinengenThe reaction mixture was concentrated under reduced pressure

Vorschrift

To a solution of ethyl 2-(2-(2-benzyloxyphenyl)ethyl)-2-methoxycarbonylaminopentanoate (2.3 g) in tetrahydrofuran (50 ml), under a nitrogen atmosphere, lithium borohydride (0.24 g) was added and the mixture was refluxed under heating for 2.5 hours. Then, a 2N dilute hydrochloric acid (5.5 ml) was added thereto and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over sodium sulfate and the solvent was distilled away under reduced pressure. The residue obtained was dissolved in methanol (30 ml), and tetrahydrofuran (1 ml) and a 5N aqueous potassium hydroxide solution (10 ml) were added thereto and the mixture was refluxed under heating for 4 days. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over sodium sulfate and the solvent was distilled away under reduced pressure. The reaction mixture was concentrated under reduced pressure to give the subject compound (1.1 g).

Quelle